title: Ligand-accelerated enantioselective propargylation of aldehydes via allenylzinc reagents.
abstract: An enantioselective propargylation of aldehydes using an allenylzinc reagent generated in situ via a zinc-iodine exchange reaction is described. The enantioselectivity is controlled by addition of a catalytic amount of readily accessible and highly tunable amino alcohol ligand L13. A wide range of aldehydes can be propargylated to afford valuable and versatile homopropargyl alcohols in good to excellent yields with high levels of enantiopurity.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Ming-Yu
authors.initials: MY
authors.lastname: Ngai
authors.forename: Guangbin
authors.initials: G
authors.lastname: Dong
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D011407:Propane / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000466:Alkadienes; D008024:Ligands; C025947:propadiene; D015032:Zinc; D011407:Propane